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Issue 10, 2019
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Transition metal catalyzed stereodivergent synthesis of syn- and anti-δ-vinyl-lactams: formal total synthesis of (−)-cermizine C and (−)-senepodine G

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Abstract

A stereodivergent and diastereoselective transition-metal-catalyzed intramolecular hydroamidation of allenes and alkynes furnishing δ-vinyl-lactams is reported. Employing a rhodium catalyst allowed for the selective synthesis of the syn-δ-lactam. Conversely, a palladium catalyst led to the formation of the anti-δ-lactam in high selectivity. The new method shows high functional group compatibility and assorted synthetic transformations were demonstrated as well as its utility for the enantioselective formal total syntheses of (−)-cermizine C and (−)-senepodine G.

Graphical abstract: Transition metal catalyzed stereodivergent synthesis of syn- and anti-δ-vinyl-lactams: formal total synthesis of (−)-cermizine C and (−)-senepodine G

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Publication details

The article was received on 10 Dec 2018, accepted on 24 Jan 2019 and first published on 24 Jan 2019


Article type: Edge Article
DOI: 10.1039/C8SC05502E
Citation: Chem. Sci., 2019,10, 3074-3079
  • Open access: Creative Commons BY-NC license
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    Transition metal catalyzed stereodivergent synthesis of syn- and anti-δ-vinyl-lactams: formal total synthesis of (−)-cermizine C and (−)-senepodine G

    J. P. Schmidt and B. Breit, Chem. Sci., 2019, 10, 3074
    DOI: 10.1039/C8SC05502E

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